This Entrepreneur Raised $70M To Build An AI-Powered B2B2B Spend And Expense Management Platform
Andrew Jamison , co-founder and CEO of Extend, chose an entrepreneurial path that didn’t involve a bold dive. Instead, he spent years quietly learning, observing, and accumulating enough pattern recognition to know when it’s finally time to build.
Extend has raised more than $70M, built deep network-level trust with card issuers, and carved out one of the most compelling B2B2B positions in fintech. In a riveting interview, Andrew shares the lessons he learned while building within one of the most complex ecosystems in financial services.
From Nowhere and Everywhere: Growing Up Across Cultures
Andrew grew up as a global citizen before the term existed. He was born in the UK to a Swedish mother and an Australian father, educated in the French school system, then later, at an English boarding school. That experience didn’t make life easier as a kid.
Andrew never quite fit in anywhere. In France, he wasn’t French. In England, he spoke with a French accent. Even in Australia, where his father was from, he was seen as “very English.” Yet what had felt like an Achilles' heel in childhood became one of his greatest assets as an adult.
“Understanding cultures, listening deeply, understanding where people are coming from, and seeing how they react to things—that’s everything in business,” Andrew says. “It builds trust and drives engagement with people. And trust is the currency startups run on.”
Traveling during his youth reinforced this. With little money, Andrew worked a wide range of jobs, from packing boxes to sheep farming, engaging with different elements of society right across the board. He ended up going to Australia because his father is Australian.
Andrew worked alongside people who had never been more than four hours from home, yet shared long conversations with him, someone who had come from the other side of the world.
Those experiences became foundational. They taught Andrew how to relate, adapt, and build trust across wildly different environments. These skills would later prove invaluable in early-stage fundraising, enterprise partnerships, and building credibility with global card networks.
The First Career: Consulting and the “Entrepreneurship of the Mind”
Andrew attended Bath University and began his career not as a founder, but in consulting, specifically in a fast-growing firm that expanded from 50 to 700 people in five years. He chose the startup in the Systems, Applications & Products in Data Processing space above three strategic consultancies.
The experience was formative. While many consultants focus on frameworks, Andrew learned something very different: coding, systems logic, and accounting, a core functional skill he picked up because of his focus on finance.
That grounding in technical thinking, along with the breadth of exposure, gave Andrew the capabilities he would later rely on as a founder. “Consulting teaches you to stay one step ahead of the client; it’s entrepreneurship of the mind,” he says.
You learn to break down big problems, challenge assumptions, and think creatively without the practical experience of having been inside the company. But you don’t get to execute. And over time, Andrew realized he wanted both.
But he was also aware that he was offering ideas to clients who clearly knew more than he did. So after Druid, rather than launching a startup like many classmates, Andrew returned to school.
At 27, Andrew found himself seated before one of Polaroid's boards, discussing how they should view their systems from a financial perspective.
Andrew also discussed the overall structure for rolling up information, outlining how to provide flexibility while still gaining key insights into the company's internal operations. H is stint at Druid had t aught him the ability to straddle different operational aspects.
The Corporate Chapter: 12 Years at American Express
Andrew went on to earn his MBA at INSEAD and, instead of launching his own business, moved to Amex, a decision that was both strategic and personal. Professionally, he wanted to understand what it was like to sit behind a truly global brand, something he never experienced in small consulting.
The consultancy had, undoubtedly, grown quickly and had gone public, but it wasn’t a real brand. Andrew wanted to experience the instant credibility people with brands could get when they walked into a room.
Personally, Andrew had grown up watching his entrepreneurial father navigate nonstop intensity and uncertainty. His father had gone through three to four different companies. He was into shop-fitting equipment at massive hypermarkets in France, from shelving to digital labels used for pricing.
By contrast, Andrew saw the stability his uncle enjoyed as an executive in Switzerland's farming sector. Amex wasn’t a retreat for Andrew; it was a training ground. He learned structure, operational excellence, culture, and how to execute within a massive global machine.
Andrew moved deeply into product and B2B, becoming part of the executive leadership program. But as Amex underwent leadership transitions and internal pressure grew for him to move from B2B into consumer roles he didn’t want, something shifted.
Andrew had the opportunity to learn different aspects of the business, but around this time, his mother fell seriously ill for the fourth time. Her illness forced him to confront the finiteness of time and the need for a sabbatical. That sabbatical changed everything.
The Breakthrough During a Time-Out: Realizing He Still Loved Building
Stepping away from corporate life gave Andrew the rarest resource founders often lack: uninterrupted time to think. “When you work for a large company, a million people tell you what you’re good at or what you should do next,” he recalls. “This was the first time I could ask: What do I actually like doing?”
The answer was simple: Andrew loved product, solving problems, and simplifying complexity and challenges. When he revisited issues inside the B2B payments ecosystem, a glaring opportunity emerged. The challenge of making technology accessible to different customer segments.
Andrew realized that virtual cards existed, but legacy systems had prevented them from reaching the companies and employees who needed them most. Ultimately, everyone used credit cards, from consumers in households to large global organizations.
Andrew recognized a significant travel opportunity by giving employees the option to spend company funds rather than use their cards and then be reimbursed. This insight became the seed for Extend.
The Birth of Extend: A Platform Layer, Not Another Issuer
Extend officially began in 2017. It addressed a significant problem in B2B spend: how to tackle the tail end of suppliers. And how to handle the massive emerging trend of subscriptions, where employees were signing up without a proper payment mechanism.
Freelancers and contractors couldn’t get corporate cards. And companies relied on reimbursements and manual processes for spend that should have been automated. In contrast, today 68% of Extend’s expenses are charged to cards, including software, web hosting, and distributed workflows.
Its processes mirror the broader trend of B2B payments shifting to virtual cards. As Andrew explains, Jira and ticket tracking are billed to his card and shared with the entire team.
The Extend Business Model
Extend caters to the small and medium-sized businesses (SMB) segment with spending and expense management tools suitable for companies with fewer than 1000 employees and less than $100M in revenue. The platform makes these tools easily accessible to their teams.
Instead of becoming a new issuer (like Ramp or Brex), Extend took a more complex but strategically powerful route. It facilitated the lives of startups with capital but no credit history who needed credit card products.
Andrew asked: Why should companies have to switch banks or card issuers just to get modern spend and expense management tools? Why can't we overlay technology onto the existing legacy stack and enable those same software workflows that help businesses become more efficient?
Digital cards with upfront controls · Automated limits, merchant restrictions, and time windows · Seamless workflows for SaaS and distributed teams · Expense management on digital or physical cards that reduces friction for users, approvers, and finance teams
The Fundraising Journey: From Friends & Family to $70M+
For someone who had spent his corporate life pitching for budgets, fundraising as a founder was a shock. “The most mind-boggling part was realizing I had no idea how to raise capital,” Andrew says.
The Failed First Pitch (and the Lesson)
One of the earliest attempts involved an investor who asked Andrew to rewrite his entire narrative the night before the meeting. He complied, but the next morning, their train was delayed by two hours, and they arrived five minutes late.
Instead of the three people Andrew anticipated, 16 investors comprising the entire executive team were in the room, and the new story felt completely unnatural. “It was a train coming off the tracks,” he recalls. He learned valuable lessons from the experience.
Always arrive a day early for meetings, and, most importantly, never let anyone else tell your story.
Your narrative must come from conviction and authenticity, not from a last-minute rewrite for someone else’s preference. Accept only good feedback and incorporate it as needed.
Storytelling is everything that Andrew was able to master. The key is capturing the essence of what you are doing in 15 to 20 slides. For a winning deck, take a look at the pitch deck template created by Peter Thiel, Silicon Valley legend (see it here) where the most critical slides are highlighted.
Remember to unlock the pitch deck template that founders worldwide are using to raise millions below.
The Friends & Family Requirement
Before any VC would invest, they wanted social proof. Coming from corporate, Andrew had no entrepreneurial background, so investors pushed him to raise $250K from friends and industry peers first. Ten people wrote $25K checks.
That capital enabled Extend to build an MVP that could actually make a purchase with a virtual card, something they demonstrated by the time they met Steve Cohen and the team at Point72 Ventures. The virtual card enabled users to make a purchase with just a card number on their phone.
The Real Breakthrough
A breakfast with Cohen turned into a 90-minute deep dive with his extended executive team. They explored Extend’s data, infrastructure, and roadmap. Three months later, Extend received its first multimillion-dollar institutional check. Eventually, the company raised over $70M in funding.
Trust and Investor Relationships Through Market Cycles
Andrew believes great investor relationships reveal themselves when the tide goes out. “In good times, everyone’s a hero. In downturns, you see people’s real personalities.”
Trust, transparency, and clean communication are essential. Investors only spend two or three days per quarter thinking deeply about your company, so founders must package information clearly, highlight the good and the ugly, and avoid storytelling that will eventually collapse under scrutiny.
“If you’ve been honest, your investors will have your back,” Andrew says. “If you’ve been dressing things up, that’s when things fall apart.”
The Future of Extend: Where Payments, Software, and AI Converge
Andrew reveals his vision for Extend that goes beyond an IPO or an acquisition. As he reveals, Extend is a B2B2B company and sits at the intersection of major shifts.
Andrew recognizes the potential of credit card networks, certain issuers, and processors that still operate around green screens, as they haven’t yet moved to the cloud. He recognizes that software platforms are moving deeper into payments and accounting, necessitating embedded spend & expense management.
As Andrew points out, some of the accounting solutions out there will need spend and expense management, because the general ledger alone won't be enough over time as others enter that space. Building trust with card networks means building trust with issuers.
Andrew sees a world where AI agents will attempt purchases, but liability models between merchants and issuers must evolve. Extend may play a critical role by becoming the intermediary that confirms intent, issues a short-lived digital card, and maintains the trust layer banks require.
Extend’s partnerships across networks and issuers, plus its B2B2B positioning, may prove strategically decisive as these worlds blend.
Advice to His Younger Self: Focus, Trust, and Verification
Andrew’s core advice to founders is simple but hard-earned: “Be really freaking focused.” Early-stage resources are scarce. The temptation to go broad is deadly. Build trust with partners and employees, but verify it.
Balance commitments, shape contracts carefully, and avoid taking all the risk when others aren’t matching it. Above all, Andrew remains deeply curious. It’s one of Extend’s core values and one he embraced long before starting the company.
Andrew loves meeting people, learning, and helping others navigate the complexities of the financial and software ecosystems. “No one builds it perfectly on the first try,” he says. “If someone needs advice on how these strategic and financial worlds fit together, I’m always happy to help.”
In Conclusion
Andrew Jamison’s path to entrepreneurship has been anything but linear. His journey spans an international childhood, multiple cultural identities, years in a fast-growing consulting firm, 12 years at American Express, a sabbatical that changed everything, and then a crash course in fundraising during the earliest chapters of Extend.
Today, Extend is one of the most respected spend and expense management platforms in the U.S. It is powering the long-overdue modernization of virtual cards, automating compliance, and helping SMBs bring financial discipline to day-to-day spend.
Growing up across cultures taught Andrew to read people, build trust quickly, and turn early identity confusion into a lifelong business advantage. · Consulting gave him “entrepreneurship of the mind,” combining problem-structuring with deep technical and accounting skills that later powered his product thinking. · Twelve years at American Express refined his execution muscle and B2B product instincts, while also showing him when big-company paths no longer fit his strengths. · A sabbatical, triggered by his mother’s illness, gave Andrew the space to rediscover his love of building products, simplifying complexity, and solving real B2B pain points. · Extend was born from a simple insight: instead of forcing companies to change banks, overlay modern virtual card and spend tools onto existing issuer infrastructure for SMBs. · Andrew’s fundraising journey—from friends-and-family capital to $70M+—taught him never to let investors rewrite his story and to prove trust with a real, working MVP. · Andrew’s core advice to founders is to be “really freaking focused,” build trust but always verify, and remember that the quality of your investor relationships is revealed when the cycle turns.
Original Version
Alejandro Cremades: Alrighty, hello everyone and welcome to the DealMakers show. So today we have an amazing guest, you know, I guess that, you know, it's it's been quite the journey, you know, close to a decade, you know, with his and with his startup.
Alejandro Cremades: And again, I mean, obviously a decade in the world of startups, imagine. And as in dark years, say if you compare to corporate, it's a lot. We're going to be talking a lot about you know the the cycles. We're going to be talking about the way to think about focus, capital raising, all of that good stuff that we like to hear when it comes to building, scaling, financing, and all the above. So brave yourself for a very inspiring conversation today.
Alejandro Cremades: And without further ado, let's welcome our guest, Andrew Jameson. Welcome to the show.
Andrew Jamison: Thanks Alejandro, looking forward to the discussion.
Alejandro Cremades: So originally, you know, from from the UK, you know, I would say, but with parents from Australia, from Sweden. So you had that interesting combination early on as part of your upbringing. Give us a walk through memory lane. How was life growing up for you, Andrew?
Andrew Jamison: It was confusing. It was confusing and I didn't really know where I was from. And I had to assimilate actually to lots of different cultures very, very quickly. It was very clear early on that that I wasn't French despite being in a French system.
Andrew Jamison: And then I went to the English system to go to boarding school. And it was really clear that I wasn't English because I spoke with a French accent. um So it kind of creates an interesting play, really, where you sort very much try to sort of figure people out and trying to understand, right, the cultural differences and how to sort of drive by that assimilation. And I think that's actually served me really well later on in life. It's a challenge in the moment.
Andrew Jamison: But actually afterwards, you realize understanding culture, understanding how people react to different things actually is super helpful in driving engagement with people, which ultimately drives trust and all these other things, right?
Andrew Jamison: they're critical ah in business. So a bit of an Achilles here when you're a kid because you want to be like everyone else, but actually a great asset when you grow up.
Alejandro Cremades: So tell us, too, about the sabbatical, and when you were traveling around, too. I mean, you were talking about cultures, getting to understand people. I mean, I think that that's everything when you are in business, right? And when you're able to really listen, listen for concerns, listen to really for for after you've been able to understood someone, what can drive that person, given maybe like where they're coming from? I mean, what kind of perspective, the travels, the cultures, you know, how do you think that has helped you to being an entrepreneur?
Andrew Jamison: Well, so I think the the best part about traveling when you're young is you have no money. um And so you're stretching everything. And so, again, you're engaging with different elements of society right across the board.
Andrew Jamison: I ended up going to Australia because my father's Australian. And I was working as a storeman and packer, right, with people were storing, you know, stacking boxes that you were sending out for shipments. I then worked on a sheep farm and actually worked there sort of in two different stints, once during the shearing season, once during the like the sort of the castration period.
Andrew Jamison: And again, working with people who'd never been more than four hours from the farm I was working on. And then I was coming from the other side of the world.
Andrew Jamison: And despite being Australian, for them, I was very English. um And obviously, I sort of tried to deflect that and said, no, I'm sort of really French because I know the Australian and and the Brits have a bad have a bad rap And of course, what had happened at that period is when the French went and shot down the Greenpeace ship.
Andrew Jamison: But all in all, look, you learn. I think you learn how to relate to people irrespective of where they come from, what part of society they come from. And again, what welcome to life. Right.
Andrew Jamison: And more relevant, probably still and inside of a startup because you're really dealing with with no brand. And so you have to build that brand, build that trust across the whole ecosystem.
Andrew Jamison: So I think really helpful in in in that guise as well.
Alejandro Cremades: Now, in your case, you know you went to a Bath for a university. and And right after that, you know you you went into consulting. So why consulting out of all things?
Andrew Jamison: Look, it's it's interesting. For me, consulting was just a way of discovering what I liked to do. And I had a choice, i actually. had a choice of joining sort of one of the three strategic consultants or actually going to work with ah actually a startup in the SAP space.
Andrew Jamison: SAP was growing really fast in ah and the mid-90s. And um I remember my father famously saying to me, it's like, why would you go into strategic consulting? You actually don't know anything. mean, it's not that he was wrong.
Andrew Jamison: And you learn different things, right? And in some respects, the first couple of years, i sort of regretted it because I realized very quickly that strategic consultant, you kind of learned about, you know, the famous two by twos, three by threes, and how to sort of like present things and do different things.
Andrew Jamison: I learned something very much more foundational going into consulting. I learned about coding. I learned about sort of the logic of things and how you have to relate things back to the database and and how that whole piece has to work.
Andrew Jamison: And then I learned actually a core functional skill, which is accounting, because I focused on finance. So I really learned two different core skills that actually have paid back again. Over time, they pay back. And I think that's, for me, the most important thing to to do and learn when when you're in the early years is learn something and learn it really, really well.
Alejandro Cremades: What about the way that you relate it to problems? Because in consulting, there's a lot of grabbing big problems, breaking them into small ones. What about your relatedness to problem?
Andrew Jamison: Well, i I think consulting gives you entrepreneurship of the mind, right? It's kind of like you're always on your feet. You're always trying to stay one step ahead of the client, right?
Andrew Jamison: And you're trying to, you don't also have the legacy of having been inside that company. And so to some extent, you're a bit of a free spirit and you can really rethink things.
Andrew Jamison: Now, the things are really stupid and you're quickly told that. But you you learn right how to to rethink problems, how to look at problems completely differently. um And that helps you to really sort of come up with real innovation in in my mind. You've got to follow it through because the problem with with consultancy is you often don't get the execution. right so it' That's why I said it's like it's it's ah it's entrepreneurship of the brain because you're constantly being challenged to stay one step ahead of the client in a discipline that they clearly know better than you in some cases.
Andrew Jamison: And then I think, you know, when I would later went into into enterprise, well, then you get sort of more entrepreneurship around execution and then you can meld the two together. And I think that's where the startup world sort really comes together for me is bring the best of the two together to sort of keep sort of driving things.
Andrew Jamison: But for me, consulting was was truly about being nimble. We were 50 people when I joined. Within five years, we'd grown to 700 people organically.
Andrew Jamison: And so i was suddenly finding myself flying to the US, sitting in front of the ah what one of the sort of the boards of of of Polaroid, talking about how they should think about their systems from a finance perspective and how that should all roll up and how they can give them flexibility and how they get insights into right what was happening inside of their company.
Andrew Jamison: And there I was, I was 27 years old. So it's a benefit of being in that small but really fast growing as you get pushed into many, many things. And I got a breadth that you wouldn't have gotten if I'd gone to one of the big sort of the big consultancy firms, you wouldn't have had that same ability to straddle across so many different things.
Alejandro Cremades: Now, for you, you did your MBA at INSEAD, and typically people that do their MBAs, you know, many of them, they end up launching their own business, right? I think in your case, you ended up going to American Express.
Alejandro Cremades: But what do you think was there for you? Why were you avoiding starting a business?
Andrew Jamison: Look, there's i mean there's two parts to that. I think the the first for me was a little bit of a comeback to when I went into consulting into a startup and it was, you know, we're 50 people. And yes, it was ah a bit more of a classic consulting, right It's about bums on seats and billings and everything else.
Andrew Jamison: But um I really missed the idea of sitting behind a massive brand.
Andrew Jamison: right I was jealous actually of of people having this brand that they could a walk in a room and instant credibility. We came from a small consultancy firm that grew really fast, went public. right but it But it was not a real brand. right And so for me, it's a little bit of that. That's one part of of the piece. right It was a little bit of me. No, I need to on understand what it's like to work for it for a big brand.
Andrew Jamison: The reality is things don't get built that way. And so my view would be like, you know, trust, verify is like a key part, not just with employees, but actually in partnerships and relationships. Right.
Andrew Jamison: You build trust, but you have to verify that there is corresponding trust, corresponding engagement with those partners. And so you don't end up as the one taking all the risk without actually there being a counterbalancing piece of of those those parties taking risk.
Andrew Jamison: And sometimes that comes in in the way that you shape contracts. Right. But sometimes it also just comes in the way of the amount of resources as you sit behind something. Right. Without there being any tangible results yet.
Alejandro Cremades: Now, for the people that are listening that would love to reach out and say hi, perhaps learn more about Xtend, what can you tell them?
Andrew Jamison: Look, I would obviously i I love having these kind of discussions.
Andrew Jamison: I love meeting new people. And that goes back to curiosity, which is one of our core values and is how I've lived my life because of the international nature of things. um They can reach out directly to me.
Andrew Jamison: i'm I'm readily available on LinkedIn. or they can reach out through email, which is andrew at paywithextend.com.
Andrew Jamison: Always really happy to engage with people who are looking for advice of, hey, how do I deal with strategics, right? How should I structure things in a financial ecosystem or in the software world?
Andrew Jamison: Those are two worlds i know really, really well, and I know how they marry themselves together and can certainly help folks avoid different pitfalls that certainly we all encounter along the way. No one builds it perfect first time around.
Andrew Jamison: And so again, always happy to help in in in that in that department.
Alejandro Cremades: Amazing. Well, Andrew, thank you so much for being on the DealMaker Show today. It has been an absolute honor to have you with us.
Andrew Jamison: Thank you very much. Really enjoyed the conversation. Thanks again.
